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01-10-2019 | Original Article

Identification of bioactive phenolics from Porana sinensis Hemsl. stem by UPLC-QTOF-MS/MS and the confirmation of anti-inflammatory indicators using LPS-induced RAW264.7 cells

Authors: Qiang Xue, Peipei Yin, Ke Li, Hang Fan, Lingguang Yang, Xinxin Cao, Liwei Sun, Yujun Liu

Published in: Inflammopharmacology | Issue 5/2019

Abstract

To characterise bioactive phenolics and confirm anti-inflammatory indicators in Porana sinensis stem, 23 phenolics were identified by UPLC-QTOF-MS/MS from crude extract (CE) prepared optimally with 80% methanol. Further fractionalisation using D101 macroporous resin resulted in predominant enrichment of total phenols and flavonoids into Fr.II. Correspondingly, the bioactive components-enriched Fr.II exhibited the lowest IC₅₀ for scavenging DPPH and ABTS and the highest oxygen radical absorbance capacity or ORAC followed by Fractions Fr.I + Fr.II, CE and Fr.I, implying that certain phenolics possessing lower antioxidant activity completely remained in CE. Anti-inflammatory tests with LPS-stimulated RAW264.7 cells showed that CE possessed the highest inhibition of NO-production followed by Fr.II and Fr.I, meaning that CE might contain compounds that expressed higher anti-inflammatory but lower antioxidant activities or possessed synergistic interactions but were not fractionated together. Quantitative determination of nine major phenolics revealed that caffeic acid and 3-, 4- and 5-caffeoylquinic acids were concentrated into Fr.I, whereas scopolin, scopoletin and 3,5-, 3,4- and 4,5-dicaffeoylquinic acids were enriched into Fr.II. Further experiments with three selected major phenolics reduced the proposed synergistic interactions. Anti-inflammatory tests of the nine major phenolics evidenced that caffeic acid and the six caffeoylquinic acids produced higher, and the three dicaffeoylquinic acids at 140 μΜ showed even more significant activities in suppressing NO-production and mRNA expression of iNOS, TNF-α, COX-2, and IL-6, suggesting that these three dicaffeoylquinic acids could be indicators of the anti-inflammatory potential of P. sinensis stem. These findings provided novel insights for potential use of P. sinensis or liana, as an important source of natural antioxidants, against inflammation.

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Apel K, Hirt H (2004) Reactive oxygen species: metabolism, oxidative stress, and signal transduction. Annu Rev Plant Biol 55:373–399. https://doi.org/10.1146/annurev.arplant.55.031903.141701 CrossRefPubMed

Broadhurst RB, Jones WT (1978) Analysis of condensed tannins using acidified vanillin. J Sci Food Agric 29:788–794. https://doi.org/10.1002/jsfa.2740290908 CrossRef

Cai H, Harrison DG (2000) Endothelial dysfunction in cardiovascular diseases: the role of oxidant stress. Circ Res 87:840–844. http://circres.ahajournals.org/content/87/10/840 CrossRefPubMed

Calixto JB, Otuki MF, Santos AR (2003) Anti-inflammatory compounds of plant origin. Part I. Action on arachidonic acid pathway, nitric oxide and nuclear factor kappa B (NF-kappaB). Planta Med 69:973–983. https://doi.org/10.1055/s-2003-45141 CrossRefPubMed

Carciochi RA, Manrique GD, Dimitrov K (2015) Optimization of antioxidant phenolic compounds extraction from quinoa (Chenopodium quinoa) seeds. J Food Sci Tech 52:1–9. https://doi.org/10.1007/s13197-014-1514-4 CrossRef

Chavan Y, Singhal RS (2013) Ultrasound-assisted extraction (UAE) of bioactives from arecanut (Areca catechu L.) and optimization study using response surface methodology. Innov Food Sci Emerg 17:106–113. https://doi.org/10.1016/j.ifset.2012.10.001 CrossRef

Chen Z, Liao L, Zhang Z, Wu L, Wang Z (2013) Comparison of active constituents, acute toxicity, anti-nociceptive and anti-inflammatory activities of Erycibe obtusifolia Benth. and Erycibe schmidtii Craib. J Ethnopharmacol 150:501–506. https://doi.org/10.1016/j.jep.2013.08.059 CrossRefPubMed

Chen Z, Liao L, Yang Y, Zhang Z, Wang Z (2015) Different fingerprinting strategies to differentiate Porana sinensis and plants of Erycibe by high-performance liquid chromatography with diode array detection, ultra high performance liquid chromatography with tandem quadrupole mass spectrometry, and chemometrics. J Sep Sci 38:231–238. https://doi.org/10.1002/jssc.201400861 CrossRefPubMed

Chunying L, Wang X, Ge G, Lian W, Yongxin L, Chengjun S (2013) Identification and quantification of free, conjugate and total phenolic compounds in leaves of 20 sweet potato cultivars by HPLC-DAD and HPLC-ESI-MS/MS. Food Chem 141:2697–2706. https://doi.org/10.1016/j.foodchem.2013.05.009 CrossRef

Clifford MN, Knight S, Kuhnert N (2005) Discriminating between the six isomers of dicaffeoylquinic acid by LC–MSⁿ. J Agric Food Chem 53:3821–3832. https://doi.org/10.1021/jf050046h CrossRefPubMed

Cui YQ, Jia YJ, Zhang T, Zhang QB, Wang XM (2012) Fucoidan protects against lipopolysaccharide-induced rat neuronal damage and inhibits the production of proinflammatory mediators in primary microglia. CNS Neurosci Ther 18:827–833. https://doi.org/10.1111/j.1755-5949.2012.00372.x CrossRefPubMedPubMedCentral

Dawa Z, Zhou Y, Bai Y, Gesang S, Bai B, Ding L (2008) Development of an HPLC-DAD-ESI-MSⁿ method for quantitative analysis of Saussurea tridactyla. J Pharm Biomed 48:1076–1081. https://doi.org/10.1016/j.jpba.2008.08.016 CrossRef

Fang X, Wang J, Hao J, Li X, Guo N (2015) Simultaneous extraction, identification and quantification of phenolic compounds in Eclipta prostrata, using microwave-assisted extraction combined with HPLC-DAD-ESI-MS/MS. Food Chem 188:527–536. https://doi.org/10.1016/j.foodchem.2015.05.037 CrossRefPubMed

Faqueti LG, Sandjo LP, Biavatti MW (2017) Simultaneous identification and quantification of polymethoxyflavones, coumarin and phenolic acids in ageratum conyzoides, by UPLC-ESI-QToF-MS and UPLC-DAD. J Pharm Biomed 145:621–628. https://doi.org/10.1016/j.jpba.2017.07.034 CrossRef

Feron O, Dessy C (2004) pathophysiological roles of nitric oxide: in the heart and the coronary vasculature. Curr Med Chem 3:207–216. https://doi.org/10.2174/1568014043355348 CrossRef

Fujioka K, Shibamoto T (2008) Chlorogenic acid and caffeine contents in various commercial brewed coffees. Food Chem 106:217–221. https://doi.org/10.1016/j.foodchem.2007.05.091 CrossRef

Furukawa S, Fujita T, Shimabukuro M, Iwaki M, Yamada Y, Nakajima Y (2017) Increased oxidative stress in obesity and its impact on metabolic syndrome. J Clin Invest 114:1752–1761. https://doi.org/10.1172/JCI21625 CrossRef

Hirakura K, Morita M, Nakajima K, Sugama K, Takagi K, Niitsu K (1997) Phenolic glucosides from the root of Pueraria lobate. Phytochemistry 46:921–928. https://doi.org/10.1016/S0031-9422(97)00371-3 CrossRef

Hsu YW, Chi KH, Huang WC, Lin WW (2001) Ceramide inhibits lipopolysaccharide-mediated nitric oxide synthase and cyclooxygenase-2 induction in macrophages: effects on protein kinases and transcription factors. J Immunol 166:5388–5397. https://doi.org/10.4049/jimmunol.166.9.5388 CrossRefPubMed

Huang WY, Cai YZ, Zhang Y (2009) Natural phenolic compounds from medicinal herbs and dietary plants: potential use for cancer prevention. Nutr Cancer 62:1–20. https://doi.org/10.1080/01635580903191585 CrossRef

Ickes GR, Fong HH Jr, Schiff PL, Perdue RE Jr, Farnsworth NR (2010) Antitumor activity and preliminary phytochemical examination of Tagetes minuta (Compositae). J Pharm Sci-US 62:1009–1011. https://doi.org/10.1002/jps.2600620635 CrossRef

Lee SR, Lee S, Moon E, Park HJ, Park HB, Kim KH (2017) Bioactivity-guided isolation of anti-inflammatory triterpenoids from the sclerotia of Poria cocos using LPS-stimulated RAW264.7 cells. Bioorg Chem 70:94–99. https://doi.org/10.1016/j.bioorg.2016.11.012 CrossRefPubMed

Longo W, Panesar N, Mazuski J, Kaminski D (1998) Contribution of cyclooxygenase-1 and cyclooxygenase-2 to prostanoid formation by human enterocytes stimulated by calcium ionophore and inflammatory agents. Prostag Oth Lipid M 56:325–339. https://doi.org/10.1016/S0090-6980(98)00058-6 CrossRef

Lotulung PD, Minarti Kardono LB, Kawanishi K (2008) Antioxidant compound from the rhizomes of Kaempferia rotunda L. Pak J Biol Sci 11:2447–2450. https://doi.org/10.3923/pjbs.2008.2447.2450 CrossRefPubMed

Markesbery WR (1997) Oxidative stress hypothesis in alzheimer’s disease. Free Radical Bio Med 23:134–147. https://doi.org/10.1016/S0891-5849(96)00629-6 CrossRef

Mihara M, Hashizume M, Yoshida H, Suzuki M, Shiina M (2012) IL-6/IL-6 receptor system and its role in physiological and pathological conditions. Clin Sci 122:143–159. https://doi.org/10.1042/CS20110340 CrossRef

Nascimento AM, Maria-Ferreira D, Dal Lin FT, Kimura A, de Santana-Filho AP, Mfp W (2017) Phytochemical analysis and anti-inflammatory evaluation of compounds from an aqueous extract of Croton cajucara Benth. J Pharmaceut Biomed 145:821–830. https://doi.org/10.1016/j.jpba.2017.07.032 CrossRef

Nathan C (2002) Points of control in inflammation. Nature 420:846–852. https://doi.org/10.1038/nature01320 CrossRefPubMed

Nathan C, Ding A (2010) Nonresolving inflammation. Cell 140:871–882. https://doi.org/10.1016/j.cell.2010.02.029 CrossRefPubMed

Pan XH, Shi XJ, Zhang XF, Jin-Ping SI (2012) Constituents of Chimonanthus salicifolius and their antioxidant activity. Chin J Exp Tradit Med Formulae 18:99–101. https://doi.org/10.13422/j.cnki.syfjx.2012.01.039 CrossRef

Protti M, Gualandi I, Mandrioli R, Zappoli S, Tonelli D, Mercolini L (2017) Analytical profiling of selected antioxidants and total antioxidant capacity of goji (lycium spp.) berries. J Pharmaceut Biomed 143:252–260. https://doi.org/10.1016/j.jpba.2017.05.048 CrossRef

Santos DR, Calixto JB, Souza GEP (2003) Effect of a kinin B₂, receptor antagonist on LPS- and cytokine-induced neutrophil migration in rats. Brit J Pharmacol 139:271–278. https://doi.org/10.1038/sj.bjp.0705236 CrossRef

Soobrattee MA, Neergheen VS, Luximon-Ramma A, Aruoma OI, Bahorun T (2005) Phenolics as potential antioxidant therapeutic agents: mechanism and actions. Mutat Res 579:200–213. https://doi.org/10.1016/j.mrfmmm.2005.03.023 CrossRefPubMed

Valko M, Rhodes CJ, Moncol J, Izakovic M, Mazur M (2006) Free radicals, metals and antioxidants in oxidative stress-induced cancer. Chem-Biol Interact 160:1–40. https://doi.org/10.1016/j.cbi.2005.12.009 CrossRefPubMed

Valko M, Leibfritz D, Moncol J, Cronin MT, Mazur M, Telser J (2007) Free radicals and antioxidants in normal physiological functions and human disease. Int J Biochem Cell B 39:44–84. https://doi.org/10.1016/j.biocel.2006.07.001 CrossRef

Wu L, Zhu E, Zhang Z, Wang Z (2005) Investigating original plant of Caulis Erycibes in Guangxi and identifying mainstream variety of Caulis Erycibes in market. Chin Trad Herb Drugs 36:1398–1400

Xue Q, Fan H, Li K, Yang L, Sun L, Liu Y (2017) Comparative evaluations on phenolic antioxidants of nine adulterants and anti-inflammation of four alternatives with their original herb Erycibe schmidtii. RSC Adv 7:51151–51161. https://doi.org/10.1039/C7RA10767F CrossRef

Yu T, Yi YS, Yang Y, Oh J, Jeong D, Cho JY (2012) The pivotal role of TBK1 in inflammatory responses mediated by macrophages. Mediat Inflamm 2012:979105. https://doi.org/10.1155/2012/979105 CrossRef

Zhang L, Ravipati AS, Koyyalamudi SR, Jeong SC, Reddy N, Smith PT, Bartlett J, Shanmugam K, Münch DG, Wu MJ (2011) Antioxidant and anti-inflammatory activities of selected medicinal plants containing phenolic and flavonoid compounds. J Agric Food Chem 59:12361–12367. https://doi.org/10.1021/jf203146e CrossRefPubMed

Zhang JY, Zhang Q, Li N, Wang ZJ, Lu JQ, Qiao YJ (2013) Diagnostic fragment-ion-based and extension strategy coupled to DFIs intensity analysis for identification of chlorogenic acids isomers in Flos Lonicerae Japonicae by HPLC-ESI-MS(n). Talanta 104:1–9. https://doi.org/10.1016/j.talanta.2012.11.012 CrossRefPubMed

Title: Identification of bioactive phenolics from Porana sinensis Hemsl. stem by UPLC-QTOF-MS/MS and the confirmation of anti-inflammatory indicators using LPS-induced RAW264.7 cells
Authors: Qiang Xue
Peipei Yin
Ke Li
Hang Fan
Lingguang Yang
Xinxin Cao
Liwei Sun
Yujun Liu
Publication date: 01-10-2019
Publisher: Springer International Publishing
Published in: Inflammopharmacology / Issue 5/2019
Print ISSN: 0925-4692
Electronic ISSN: 1568-5608
DOI: https://doi.org/10.1007/s10787-018-00558-1

At a glance: The STEP trials

Springer Medicine

Identification of bioactive phenolics from Porana sinensis Hemsl. stem by UPLC-QTOF-MS/MS and the confirmation of anti-inflammatory indicators using LPS-induced RAW264.7 cells

Abstract

At a glance: The STEP trials

Springer Medicine

Abstract

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